Family-friendly holiday rentals in Callicoon

We had a wonderful time at this place for our mini moon. It was relaxing, beautifully decorated, well stocked with everything you need! The hosts were very responsive. We would stay here again in a heartbeat! For anyone coming from NYC we stoped at Pho Tibet in New Paltz for lunch on the way home and the food was amazing!

This A-frame escape was exactly what I needed — the perfect break from the city. The place is beautifully designed, cozy, and filled with thoughtful touches. The jacuzzi was absolutely incredible, especially under the stars at night, and the A-frame structure made the whole stay feel like a peaceful retreat.

This was our second stay with Joe and Amy hosting us and it was lovely yet again! They are extremely friendly and responsive. The place is serene and gorgeous. We absolutely adore the chickens and thoroughly enjoyed the fishing spot they told us about. It’s a beautiful place to unwind and relax away from city life. We plan to return again!

We had such a great stay at Eugene’s place! The house was perfect for our group — spacious, comfortable, and full of fun things to do. We especially loved the private theatre, the hot tub, and especially the sauna — such a great touch! The volleyball net was a hit, and there were tons of games in the closet that kept us entertained. The kitchen was well-stocked and roomy enough for us to cook meals for our large group, and there were plenty of different areas to hang out in, everyone could find their own space to relax. The towels were plentiful (huge plus) and having access to the washer and dryer came in handy during our stay. Eugene was a fantastic host — super friendly, very responsive, and just really helpful all around. We also got to enjoy a few deer sightings right in the yard, which felt magical. We visited the nearby alpaca farm and did the Beer Mountain hike, which was a nice outing. All in all, a wonderful stay. Would absolutely come back. Thank you Eugene!

The house is spacious and elegant. The wooded lot has a pretty creek a little way from the house. We took some walks through the snowy woods and roads beyond the house and could have kept going for a long time - the mountain is peaceful and beautiful. The owners live a few doors down and came by to help set us up before a major snow storm. We had a really nice time.

It is clear Adam and Chrissy take care of this place like their own home. I cannot emphasize enough how wonderful this place is. Perfectly equipped, yet doesn’t feel cluttered. Cozy, tasteful, full of wonderful little details, clear instructions and good vibes overall. Location is amazing and perfect for days of reflection / retreat in the mountains. Has all you need in the kitchen, plenty of books, board games, movies, records, even Atari and an AMAZING outdoor spa. Best of all is the water stream running below: natural forest + running water sounds - not even headspace can give you this to perfection. Outdoor seating area also lovely. I felt at home from beginning to end. Hosts incredibly responsive and helpful. Can’t wait to return !

Wonderful space with lots of privacy. Would stay again in a heart beat!

We enjoyed our stay at Caitlin’s cabin! Communication was great. The place was spotless. I loved the many plants inside and the peaceful surrounding area filled with many deers visiting the yard. Soaking in the hot tub was so relaxing at night. And the fire pit outside was a really nice touch to our stay. I recommend this cabin and host! We didn’t get to enjoy the kayaks because of the weather, but it’s really nice that it was an option! Thank you!!

Another great stay at Alex’s place, we’ll stay again if we’re back in the area!

Jen & Caroline’s place was exactly as described and just what we needed for a Catskills getaway. We even got to see a hometown Saint Patrick’s day parade that Jen and Caroline recommended - and allowed us to check out a little late so we could attend. So sweet. Would recommend for your Catskills vacation.

Host was very accommodating and generous . Please brings you back to simpler day just what we needed to get away from the city

It's a magical location with a beautiful forest and reservoir view.

Beautiful chalet with even better views - perfect for a calm and peaceful get away from the city, near hiking trails and 7 min from town for restaurants, had a great weekend and hope to be back soon

My boyfriend and our 2 pups enjoyed our time here! The place was mostly stocked with what we needed (no lighter for fire pit or coffee filters that we could find (but it rained and k-cups were provided), which neither are a big deal, but things we didn’t think to pack - so pack those if you’d need them!), it was clean, and we enjoyed the location for hiking / fishing and good food! We’d stay here again!

A super stylish, immaculate and serene cottage with spectacular mountain views. This absolute gem is perfect for relaxing, decompressing and exploring the Catskills. The beds and bedding are super comfortable, kitchen is well stocked, and the sight line to mountains is a visual feast. The windows are plentiful for gentle, fresh breezes wafting throughout the home yet A/C and heat work well when needed. We built a fire and star gazed surrounded by a field of fireflies. The hum of bees in the morning sun while having coffee on the deck is a delight. There’s a thorough and helpful guide/manual and the hosts are extremely responsive. Be sure to spin some records - we found the Donna Summer Greatest Hits double album - plenty of room for dancing around. Will most certainly be back!

what a great location! we tried cafe mornings, country store & bread alone! visit foodtown for groceries and charcoal- and you don't have to leave this beautiful location! if you you do a lot of hikes to bring your dog too!

Had a great time at the cozy cabin. It's a cabin but still has some nice amenities. Location is somewhat close to road, you can hear occasional cars go by. Still, back by the pond it feels like being away from it all. I had a blast hiking local trails and enjoying the foliage.

This is a beautiful, secluded house that makes you feel that you're deep in the Poconos. Convenient drive to the local grocery store and other local restaurants. The communications with our hosts were clear and concise and they gave easy to follow instructions on where to go once you check in at the gatehouse. 5 stars, would stay again!

Brian was an excellent host! He has a lovely home and it was perfect for our long weekend with our family. Absolutely beautiful outdoor surroundings with two fire pits. Lovely decor throughout his home and even a little coffee closet (so cute!). Brian was so accommodating and responsive to our many requests and always very helpful.

I stayed at this cozy barn unit for a month, and it was wonderful. The apartment was spotless, incredibly comfortable, and perfect for working from home or relaxing on the couch. The layout was thoughtfully designed, and the snowy landscape made it feel like a winter wonderland—I even saw deer in the backyard! The location was quiet yet close to charming downtown areas with craft coffee shops, grocery stores, and boutique shops. The property matched the listing perfectly, and everything felt just as described. The host was fantastic—responsive, accommodating, and quick to address a couple of small issues while offering great local recommendations. The bed, couch, and desk chair were all super comfortable, making it easy to settle in and enjoy my stay. I’d definitely book this place again and highly recommend it to anyone looking for a peaceful and cozy getaway.

We had the best family vacation at beautiful lake house. The place is very spacious and neat, and the best part is that they let us use the canoe and bikes. Julia, the property manager was very friendly and respond fast. I recommend this place!

Trish was an amazing host. Her home is beautiful and was such a wonderful experience. I can’t thank her enough for her help with a last minute booking and helping us out. I hope to come back sometime soon! It’s a dream house and property!

My partner and I stayed at Cynthia’s place for a last minute trip upstate. The cottage was simple and basic, just as expected. Our dog loved the open green space. We made use of the pool and tennis court. The place was near a couple of excellent restaurants in Mountain Dale. Overall, a nice experience. Thanks Cynthia!

I stayed here for one night to celebrate my graduation and birthday, and it was absolutely perfect! The place looks even better than the pictures! Every room was beautiful, clean, and spacious, with more than enough room for everyone. The amenities were amazing and made the stay feel extra special. Nick, the host, was so nice and welcoming, and he was happy to respond to any questions I had. I would definitely come back again. Highly recommend!